89 John Perry Road
Eastford, Connecticut 06242
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 4,538
- Acres
- 3.00
- Year Built
- 1800
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
The Benjamin Bosworth House has been part of Eastford's landscape for more than two centuries, and there is still nothing quite like it. Set on 3 acres, this Federal-style home, completed around 1800, offers 4,538 square feet, 4 bedrooms, 2.5 baths and 11 fireplaces. Its defining feature is a rare full-height monitor, once used as a Masonic meeting hall, with built-in benches and fireplaces. Throughout the house, hand-carved woodwork, historic finishes and generously scaled rooms tell the story of its past. The main level includes a formal dining room, parlor, sunlit sitting room, kitchen, studio and workshop, with additional flexible space upstairs. Since purchasing the home in May, the current owner has continued restoration work, including new lime plaster in the parlor and second-floor hall, a retiled upstairs bath and fresh paint in several rooms. Listed on the National Register of Historic Places, this is a remarkable opportunity for someone who appreciates early American craftsmanship and wants to carry its story forward.
Key Facts
- City/Town
- Eastford
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1800
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 4,538 sq ft
- Lot Size
- 3.00 acres
- Property Taxes
- $6,744 / Annually
Market Snapshot
The Eastford Market
Single Family · trailing 12 months
Active Listings
2
6 under contract
Median List Price
$497,000
2 active listings
Median Closed Price
$375,000
19 sales
Median Days on Market
4
2 active listings
Median $ / Sq Ft
$124
2 active listings
Sale-to-List Ratio
100.0%
19 sales
How this home compares
List Price
$625,000
vs $497,000 median
25.8% above median
Price / Sq Ft
$138
vs $124 median
11.3% above median
Days on Market
0 days
vs 4 days median
4 days fresher than median
Based on 2 active and 19 closed sales (trailing 12 mo) of single family in Eastford. Source: SmartMLS · As of September 29, 2026.
Location
89 John Perry Road, Eastford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$3,337
- Property Taxes$562
- Insurance$208
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Eastford
- Neighborhood
- N/A
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1800
- New Construction
- No/Resale
- Living Area
- 4,538 sq ft
Schools
- Elementary
- Eastford
- High
- Woodstock Academy
Interior
- Heating
- RadiatorSteam
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 11
- Laundry
- Main Level
- Laundry Location
- Laundry room off kitchen
- Appliances
- Refrigerator
- Basement
- FullFull With Walk-Out
- Interior Features
- Cable - AvailableElevator
Exterior & Lot
- Lot Size
- 3.00 acres
- Zoning
- RES
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- Yellow
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- Porch-ScreenedPorch
- Lot Description
- Sloping Lot
Listing & Financials
- Property Taxes
- $6,744 / Annually
- Days on Market
- 0
- MLS #
- 24210501
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/29/2026 at 2:30 AM UTC.